My Worst Date Podcast LLC
My Worst Date
Ever been on a crazy bad date? You're not alone! Join hosts and best friends Keegan Winfield, Christina Conner, and Cassi Young-Paxton as they dish about pop culture, relationships, true crime and share stories from listeners and their past of the worst dating disasters.
Author
My Worst Date Podcast LLC
Category
Podcast website
Latest episode
Jul 8, 2026
Where to listen?
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Episodes
Shorty - 41 03.01.2022 18:38
In this bite-sized episode, the girls play would you rather about New Year's shenanigans, scream about a date that eats trash, roll their eyes about a very contrary date, and laugh about a date that skipped several steps. They also share a story of drunken downtown maintenance, a date that had a surprise boyfriend and a story of a guy with a special tattoo. Got a story to share? Go to http://www...
Cautiously Optimistic 29.12.2021 1:22:51
This week Keegan, Cassi and Christina talk about Christina's divorce party and making it through hard times with great friends. The final FMK of the year is on our 2021 crushes Oscar Isaac, Anderson Paak, and Taika Waititi. Going into the bad date stories, Keegan shares a story of a date that turned out to be a friend's POS ex, Cassi shares a story of a date that is hiding a pretty monstrous side...
Hardcore Holidays 22.12.2021 1:09:41
This week Keegan, Cassi and Christina talk about Ben Affleck and fake relationships, and play FMK with holiday songs Carol of the Bells, Santa Baby and All I Want For Christmas is You. Going into the bad date stories, Christina shares a story of the absolute worst Christmas gift, Keegan shares a story of a power point from an incel and Cassi shares another story of flirty fishing. Christina wraps...
Hi Mommy! 15.12.2021 1:32:21
This week Keegan, Cassi and Christina talk about the SATC revival And Just Like That...all the feelings, drama and Pelotons! This leads into the FMK where the girls have to decide between SATC boyfriends Big, Harry and Steve. Going into the bad date stories, Cassi shares a story about a date with a startling habit, Keegan shares a doozy about double dating brothers and Christina shares a story of...
The Bar is in Hell 08.12.2021 1:21:22
This week Keegan, Cassi and Christina talk about the most common bad date had where you just listen to them spout off random opinions as facts and new developments in robots. This leads to an FMK of hot robots: David from Prometheus (Michael Fassbender), Rick Deckard from Blade Runner (Harrison Ford) and the Terminator from T2 (Arnold Schwarzenegger). Going into the bad date stories, Keegan shares...
Shorty - 40 06.12.2021 24:04
In this bite-sized episode, the girls play would you rather about dating someone that hates the holidays or someone that loves them but runs a 5k the day after Christmas, talk about a date talking to your mom about whale semen, get mad at a forceful date, and laugh at a date with mistaken identity. They also talk about a date with his foot in his mouth, scream about interfering parents, and get sc...
Chaos Goblins 01.12.2021 1:12:19
This week Keegan, Cassi and Christina talk about candles during sex and Keanu Reeves and Winona Ryder being "married". The FMK this week is inspired by a tweet about the new "it" guys Machine Gun Kelly, Travis Barker and Pete Davidson. Going into the bad date stories, Christina shares a story about a date in the parking lot that gets into a serious misunderstanding, Keegan shares a story of a holi...
A Light Google 24.11.2021 1:41:28
This week Keegan, Cassi and Christina talk about the new audio feature on Hinge and the resurgence of the Taylor Swift and Jake Gyllenhaal break up from the rerelease of her album, Red. The FMK this week is unconventially attractive actors who play characters you shouldn't be attracted to: James Gandolfini, Steve Buscemi and Tilda Swinton. Going into the bad date stories, Cassi shares a story of a...
Sloppy Nights 17.11.2021 1:41:24
This week Keegan, Cassi and Christina talk about weird things partners have done in bed asking if it feels good, and then dive into an impossible FMK: Paul Rudd, Ryan Reynolds and Keanu Reeves. An agonizing choice for sure! Going into the bad date stories, Keegan shares a listener story of a shame receipt involving young love and poetry, Christina shares a listener story of a seriously sloppy make...
Poor Thomas 10.11.2021 1:39:01
This week Keegan, Cassi and Christina talk about Pete Davison and Kim Kardashian rumors and the Kardashian family impact on beauty standards and social media. The FMK this week is short kings Elijah Wood, Mark Wahlberg and Kendrick Lamarr. Going into the bad date stories, Christina shares a listener story of an awkward texting mishaps, Keegan shares a horror story of meeting the family and Cass s...
An Amuse Bouche of Criminality 03.11.2021 1:22:10
This week Keegan, Cassi and Christina talk about issues with women and healthcare and medical gaslighting. They also answer the question posed by a TikTok on whether or not someone buying you a drink is cheating. The FMK this week is rock zaddies Lenny Kravitz, Pete Townsend, and Paul McCartney. Going into the bad date stories, Cassi shares a listener story of an 80s teenage ninja saga, Keegan te...
Shorty - 39 01.11.2021 21:53
In this bite-sized episode, the girls play would you rather about being on a date with someone that brings their mother or their ex, laugh at a little sister date crashing, giggle at a lame revenge date and gasp at a date that ended early. They also talk about a date with front row seats for a break up, rolls their eyes at a date that has to carry everything, especially the conversation, and scr...
You're Not Cool 27.10.2021 1:20:43
This week Keegan, Cassi and Christina talk about Megan Fox's wild instagram post about Machine Gun Kelly and their own cringeworthy Tumblr teenage posts. This leads into our FMK on spooky bad boys Beetlejuice, Jareth the Goblin King, and Captain Jack Sparrow. Going into the bad date stories, Keegan shares a story of a shockingly blunt date at a fancy restaurant, Cassi shares the story of a terrib...
A Woman Having a Good Time 20.10.2021 1:11:59
This week Keegan, Cassi and Christina have to discuss "floating" and "soaking". This is a bananas workaround that cannot be a real thing, but is. They also discuss a real life cult that believes they are wives of Severus Snape from Harry Potter. This leads into our FMK on antiheroes Deadpool, Snape and Loki. Going into the bad date stories, Christina shares the story of a date with the saddest ro...
Fresh Ghosts 13.10.2021 1:19:28
This week Keegan, Cassi and Christina have to discuss @elysemyers on TikTok and her terrifying story of a worst date with 100 hard shell tacos. There are a lot of questions, but the biggest one remains, why??? This leads into our FMK on fast food taco places Taco Bell, Del Taco and Chipotle. Going into the bad date stories, Cassi shares a story of a problematic date telling a very dark story and...
Not Even One Night 06.10.2021 1:27:22
This week Keegan, Cassi and Christina talk about the Grimes and Elon Musk breakup, depression, and Controlling Britney Spears. #freebritney! Heading into the FMK for the week, the girls decide what celebs they think are not great in bed: Jimmy Fallon, Vin Diesel and Joe Rogan. This is all alleged but the perception is there! Going into the bad date stories, Keegan shares a story of a date with an...
Shorty - 38 04.10.2021 22:11
In this bite-sized episode, the girls play would you rather about being on a date with someone that's too drunk or too high, laugh at a very clumsy date, scream about a fiery date and get awkward with a date that only wants to talk shop. They also talk about a date on the most inappropriate location, giggle about a very high date, and cringe about a motion sick date trying to make a move. They c...
Take A Break 29.09.2021 1:21:12
This week Keegan, Cassi and Christina chat about LulaRich, the Amazon Prime documentary about LulaRoe, and the issues they have with the bossbabe culture. This leads to talking about the pressure women face to find their "happy ending", meaning marriage and kids and the hope that we can redefine that. Heading into the FMK for the week, the girls do a listener suggestion of the popular dating apps:...
Inquiring Minds 22.09.2021 1:23:56
This week Keegan, Cassi and Christina talk about the Gabby Petito case and that fear of not knowing who you're sleeping next to. How has quarantine changed people, changed their relationships? They also get into Met Gala looks, and how Kim Kardashian is a whole vibe. Heading into the FMK for the week, the girls do their least favorite Met Gala looks: Debbie Harry, Ciara and Frank Ocean. Someone pl...
Who You Gonna Call? 15.09.2021 1:25:53
This week Keegan, Cassi and Christina talk about the John Mulaney and Olivia Munn baby news and how it feels to watch your ex move on quickly. This leads to a conversation about cancelled celebrities who need a second look. Heading into the FMK for the week, the girls do previously cancelled celebs: Ashley Judd, Winona Ryder and Corey Feldman. Because of the context, they eliminated the Kill choic...
Doctor Who? 08.09.2021 1:14:28
This week Keegan, Cassi and Christina talk about reasons why someone didn't get a second date. They also have a conversation about shows that have been saved by their fans. It's a good idea if Jeff Bezo likes your show and wants to know how it ends! Heading into the FMK for the week, the girls do their sci-fi crushes: Lando Calrissian (Billy Dee Williams), Dr. Who (the David Tennant version) and W...
Shorty - 37 06.09.2021 23:53
In this bite-sized episode, the girls discuss sleep incompatibility and cuddling, play would you rather about either crying or screaming at sex, cringe at a date trying to show off and get heated about a car with a surprise rodent. They also talk about a date with a fetish for casts, laugh about a date with a shitty excuse, scream about a date trying to sneak something super weird while sleeping...
Not Like The Other Girls 01.09.2021 1:37:06
This week Keegan, Cassi and Christina talk about burning bridges and the hate you have for people your friends hate. They also have a conversation about what movies influenced your love ideals, either for the better or the worse. Whether it was those 90s bet movies or the manic pixie dream girl trope, all of those messages crept their way into past relationships....even if it means you had to watc...
Make Good Choices 25.08.2021 1:15:52
This week Keegan, Cassi and Christina talk about the new relationship between Channing Tatum and Zoe Kravitz. The conversation leads us to FMK different Channing Tatum characters: Jupiter Ascending, Magic Mike and 21 Jump Street. It's a treat for the 6 people who have actually watched Jupiter Ascending. Going into the bad date stories, Keegan tells a horror story from a listener about a man child...
Just Say No 18.08.2021 1:31:59
This week Keegan, Cassi and Christina answer a question from a listener about how to flirt. This leads to a conversation about celebrities or people that get married multiple times. Who's got the money or time to plan all these shindigs? The conversation leads us to FMK different Will Smith characters: Deadshot, Hitch and I Am Legend. Definitely disagree on some things, but all agreed that Will Sm...
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